Oxalyl chloride → 5-(Methylsulfanyl)-1,3,4-oxadiazole-2-carbonyl chloride

HRID 1414233Notes

Reaction equation

HRID 1414233 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].[CH3:7][S:8][C:9]1(C([O-])=O)OC[N:11]=[N:10]1.[K+]>C1C=CC=CC=1.[Hg]>[CH3:7][S:8][C:9]1[O:3][C:2]([C:1]([Cl:6])=[O:5])=[N:11][N:10]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 70634320HCID 70634320, compound

Product 1

HCID 135447285-(Methylsulfanyl)-1,3,4-oxadiazole-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 241BenzeneSolvent2×

Procedure

A solution of oxalyl chloride (2.57 ml., 0.03 mole) in benzene (15 ml.) was added dropwise to a refluxing suspension of potassium 5-methylthio-1,3,4-oxadiazole-5-carboxylate (3.96 g., 0.02 mole) in benzene (50 ml.). After the addition, the mixture was stirred at reflux for one hour. Filtration and evaporation left the acid chloride; distillation gave 1.86 g. (52%); B.P. 65°-69° C. at 0.05 mm. of mercury.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for one hour
  3. filtrationFiltration and evaporation
  4. waitleft the acid chloride
  5. distillationdistillation
  6. customgave 1.86 g

Sources & evidence

ORD record
ord-4d81efb001b74afe9c19522b8967e76c
Source dataset
uspto-grants-1977_01
Patent number
US04001238

Reaction notes

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